THE BRAZEN CAREERIST- Naughty guide: Let's discuss weird work topics

There are some things about work that are difficult for even me to write about. These are the issues that I have not quite worked out for myself. I wonder if I am normal in these areas? Maybe no one is talking about them, but they are thinking still. Here are three workplace issues that I wonder if you think about as much as I do.

1. Having a huge crush on your boss.

Seriously, I have never worked for a guy for more than three months without developing a huge crush. This is, in part, because I have been fired so often that any guy I did not last three months with probably fired me and probably had no synergy with me.

But the bosses I did well with, I developed mad crushes on. All of them. Of course, I have worked always for good-looking men. (But, statistically, most of us have good-looking bosses.) I have always grown more attracted to my boss as we did better in the business. And I have noticed that it snowballs: The better we did together, the more attracted I became, and the more attracted I was, the more tuned in I was to his thinking, and that made me better at work.

I have never slept with a boss. I like to think that I would have said no. (Though I'm not sure.) But I did find, through advice and personal experience, that women who work for men who are attracted to them have a little bit of power from that attraction. But the women lose that power if they give in and sleep with the guy. This seems right.

2. Not knowing whether a meeting is a date.

Recently I met a guy for lunch. On the weekend. He is a big name. Big enough that developers have wet dreams about meeting him in person. Big enough that one of the first things he said to me when I met him was that I can't use his name. So I'm not telling who he is, but it's just as well, because while his email was innocuous, a friend told me, "This guy wants to get in your pants."

But it's nearly impossible to tell for sure. I am a single woman, and when I get an email from a single guy who just wants to get together and meet because we both know we are both interesting, well, who knows if it is a date or not? And really, it doesn't matter. I mean, we do the same thing at a business lunch and a date: figure out if we like talking enough to talk more.

3. Figuring out what to wear to the office at 10pm.

Since I'm at a startup, and I also work odd hours, I find myself in the office at odd hours. For example, I often leave work in the afternoon to pick up my kids, so it seems reasonable that if people want to meet with me later, after the kids are in bed, I say yes.

But I go running at night. And one thing I know about myself is that if I don't put on running clothes before 9pm, I'll never actually go running. So what do I wear to a 10pm meeting? Running clothes, of course.

But I feel a bit guilty. Of course workout clothes are not appropriate for work. But it's 10pm. And the people at work at 10pm are often about to spend the night at the office, and they'll smell bad the next morning. And that's not appropriate either, but just in a different way.


Penelope Trunk has started several companies and worked for many more.